Isolation of Phomopsolide A and 6(E)-Phomopsolide A as Antimycobacterial Products from an Unidentified Endophyte of the Canadian Medicinal Plant Heracleum maximum
Free accessResearch articleFirst published online October, 2015
Isolation of Phomopsolide A and 6(E)-Phomopsolide A as Antimycobacterial Products from an Unidentified Endophyte of the Canadian Medicinal Plant Heracleum maximum
An extract of an unidentified endophyte from the Canadian medicinal plant Heracleum maximum exhibited a unique metabolomic profile and significant antimycobacterial activity against Mycobacterium tuberculosis H37Ra. Bioassay guided fractionation of the extract led to the isolation of phomopsolide A (1) and 6(E’)-phomopsolide A (2). This is the first report of antimycobacterial activity for 1 and 2.
WHO, (2014) Global Tuberculosis Report 2014, WHO Press, Geneva, Switzerland, pp.
2.
LienhardtC, RaviglioneM, SpigelmanM, HafnerR, JaramilloE, HoelscherM, ZumlaA, GheuensJ. (2012) New drugs for the treatment of tuberculosis: Needs, challenges, promise, and prospects for the future. Journal of Infectious Diseases, 205, S241–S249
LiH, DoucetB, FlewellingAJ, JeanS, WebsterD, RobichaudGA, JohnsonJA, GrayCA. (2015) Antimycobacterial natural products from endophytes of the medicinal plant Aralia nudicaulis. Natural Product Communications, 10, 1641–1642
5.
FlewellingAJ, BishopAI, JohnsonJA, GrayCA. (2015) Polyketides from an endophytic Aspergillus fumigatus isolate inhibit the growth of Mycobacterium tuberculosis and MRSA. Natural Product Communications, 10, 1661–1662
6.
ClarkTN, BishopAI, McLaughlinM, CalhounLA, JohnsonJA, GrayCA. (2014) Isolation of (-)-avenaciolide as the antifungal and antimycobacterial constituent of a Seimatosporium sp. endophyte from the medicinal plant Hypericum perforatum. Natural Product Communications, 9, 1495–1496
7.
GrayCA, JohnsonJA, WebsterD. (2013) Canadian traditionally used medicinal plants: can they play a role in antituberculosis drug development?Future Medicinal Chemistry, 5, 853–855.
8.
StierleDB, StierleAA, GanserB. (1997) New phomopsolides from a Penicillium sp. Journal of Natural Products, 60, 1207–1209
9.
GroveJF. (1985) Metabolic products of Phomopsis oblonga. 2. Phomopsolide-A and phomopsolide-B, tiglic esters of 2 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones. Journal of the Chemical Society-Perkin Transactions1, 865–869.
10.
DaiJQ, KrohnK, GehleD, KockI, FlorkeU, AustHJ, DraegerS, SchulzB, RheinheimerJ. (2005) New oblongolides isolated from the endophytic fungus Phomopsis sp from Melilotus dentata from the shores of the Baltic Sea. European Journal of Organic Chemistry, 4009–4016
11.
HornWS, SimmondsMSJ, SchwartzRE, BlaneyWM. (1996) Variation in production of phomodiol and phomopsolide B by Phomopsis spp. Mycologia, 88, 588–595
12.
GoddardM-L, MottierN, Jeanneret-GrisJ, ChristenD, TabacchiR, Abou-MansourE. (2014) Differential production of phytotoxins from Phomopsis sp from grapevine plants showing esca symptoms. Journal of Agricultural and Food Chemistry, 62, 8602–8607
13.
Abou-MansourE, GoddardML, MottierN, ChristenD, TabacchiR. (2007) Toxins and secondary metabolites from the fungus Phomopsis spp., a pathogen responsible for vine excoriosis. Phytopathologia Mediterranea, 46, 111–111.
14.
StierleAA, StierleDB, MitmanGG, SnyderS, AntczakC, DjaballahH. (2014) Phomopsolides and related compounds from the alga-associated fungus, Penicillium clavigerum. Natural Product Communications, 9, 87–90.
15.
YuanL, LinX, ZhaoP-J, MaJ, HuangY-J, ShenY-M. (2009) New polyketides from endophytic diaporthe sp XZ-07. Helvetica Chimica Acta, 92, 1184–1190.
16.
FlewellingAJ, JohnsonJA, GrayCA. (2013) Isolation and bioassay screening of fungal endophytes from North Atlantic marine macroalgae. Botanica Marina, 56, 287–297.
17.
O'NeillTE, CarpenterCD, LiH, WebsterD, JohnsonJA, GrayCA. (2014) Optimisation of the microplate resazurin assay for screening and bioassay guided fractionation of phytochemical extracts against Mycobacterium tuberculosis. Phytochemical Analysis, 25, 461–467
18.
CarpenterCD, O'NeillT, PicotN, JohnsonJA, RobichaudGA, WebsterD, GrayCA. (2012) Anti-mycobacterial natural products from the Canadian medicinal plant Juniperus communis. Journal of Ethnopharmacology, 143, 695–700.
